1,4-Naphthoquinone Derivative as Efficient Photolabile Molecule: Concise Synthesis and Photorelease of Various Functional Compounds DOI
Tsuyoshi Kawai, Tsumoru Morimoto, Haiying Liu

и другие.

Synthesis, Год журнала: 2022, Номер 55(01), С. 150 - 158

Опубликована: Авг. 29, 2022

Abstract We report on a series of 1,4-naphthoquinone (NQ)-based photolabile molecules, including various functional compounds to be released under light irradiation. They were efficiently prepared from common precursor for photoremovable masking group, by attaching different such as alcohols, amines, and acids concise synthetic method. Synthesis the was optimized two-step reactions also one-pot reaction involving 1,4-addition successive aldol NQ. The compounds, amines carboxylic, phosphoric, sulfonic acids, masked with NQ-based successfully irradiation UV (λ = 360 nm) in high yields (>90%).

Язык: Английский

Photocleavable Ortho-Nitrobenzyl-Protected DNA Architectures and Their Applications DOI Creative Commons
Michael O’Hagan, Zhijuan Duan, Fujian Huang

и другие.

Chemical Reviews, Год журнала: 2023, Номер 123(10), С. 6839 - 6887

Опубликована: Апрель 20, 2023

This review article introduces mechanistic aspects and applications of photochemically deprotected

Язык: Английский

Процитировано

62

Oligonucleotides: evolution and innovation DOI Creative Commons
A. Mohammed, Danah AlShaer, Othman Al Musaimi

и другие.

Medicinal Chemistry Research, Год журнала: 2024, Номер unknown

Опубликована: Ноя. 21, 2024

Abstract Oligonucleotides, comprising single or double strands of RNA DNA, are vital chemical compounds used in various laboratory and clinical applications. They represent a significant class therapeutics with rapidly expanding range uses. Between 1998 2023, 19 oligonucleotides have received approval from the U.S. Food Drug Administration (FDA). Their synthesis methods undergone evolution over time. This review examines several oligonucleotide techniques, including phosphodiester, phosphotriester, phosphoramidite approaches. It begins discussion an early method involving phosphoryl chloride intermediate, which proved unstable prone to hydrolysis. The then transitions solid-phase method, uses polymer resins as solid support, emphasizing its advantages both phosphotriester techniques. is followed by exploration recent advancements enzymatic synthesis, concluding on modifications bases, sugars, backbones designed improve their properties therapeutic potential.

Язык: Английский

Процитировано

4

The effect of neighbouring group participation and possible long range remote group participation in O-glycosylation DOI Creative Commons
Rituparna Das, Balaram Mukhopadhyay

Beilstein Journal of Organic Chemistry, Год журнала: 2025, Номер 21, С. 369 - 406

Опубликована: Фев. 17, 2025

Stereoselective glycosylations are one of the most challenging tasks synthetic glycochemists. The protecting building blocks on glycosides contribute significantly in attaining required stereochemistry resulting glycosides. Strategic installation suitable groups C-2 position, vicinal to anomeric carbon, renders neighbouring group participation, whereas distal C-3, C-4, and C-6 positions often claimed exhibit remote participation with carbon. Neighbouring being widely studied help glycochemists design protocols for multistep synthesis complex oligosaccharides turn, standardise process glycosylation towards a particular stereochemical output. While has been quite effective achieving produced glycosides, exhibits comparatively less efficacy complete stereoselectivity reactions. Remote is still highly debated topic scientific community. However, implementing participating role reactions practised achieve better stereocontrol facilitate formation synthetically glycosidic linkages.

Язык: Английский

Процитировано

0

Photolabile ortho‐Nitro‐Benzyl Carbonate as a Permanent Hydroxyl Protecting Group for the Synthesis of Digalactosyl Diacylglycerol DOI
Jibin Zheng, Hongyu Chen,

Jintao Shang

и другие.

Chinese Journal of Chemistry, Год журнала: 2024, Номер unknown

Опубликована: Окт. 16, 2024

Comprehensive Summary Traditional protecting groups are often removed under harsh conditions with potentially hazardous reagents, thereby impeding the convenient synthesis of oligosaccharides and glycosides. Herein, we present to utilize photolabile ortho ‐nitro‐benzyl carbonate ( o NBC) as a permanent hydroxyl group for stereocontrolled The Ph 3 PO‐modulated glycosylation strongly disarmed per‐ O ‐ NBC‐protected glycosyl ynenoates preferred afford glycosides excellent α‐selectivities via β‐phosphonium transition state. Based on NBC‐mediated galactosylation, glycolipid digalactosyl diacylglycerol (DGDG) containing six double bonds two esters was achieved in straightforward manner.

Язык: Английский

Процитировано

2

Photo-labile BODIPY protecting groups for glycan synthesis DOI Creative Commons

Sabrina Leichnitz,

Komadhie C. Dissanayake,

Arthur H. Winter

и другие.

Chemical Communications, Год журнала: 2022, Номер 58(75), С. 10556 - 10559

Опубликована: Янв. 1, 2022

Protective groups that can be selectively removed under mild conditions are an essential aspect of carbohydrate chemistry. Groups by visible light particularly attractive because carbohydrates transparent to light. Here, different BODIPY protecting were explored for their utility during glycan synthesis. A group bearing a boron difluoride unit is stable glycosylations but cleaved with green as illustrated the assembly trisaccharide.

Язык: Английский

Процитировано

9

Orthogonal Deprotection of Photolabile Protecting Groups and Its Application in Oligosaccharide Synthesis DOI
Guoqiang Liu, Yingle Feng, Qi Zhang

и другие.

Organic Letters, Год журнала: 2024, Номер 26(27), С. 5746 - 5751

Опубликована: Июль 2, 2024

We herein report for the first time inter- and intramolecular orthogonal cleavage of two

Язык: Английский

Процитировано

1

C2‐Cyanomethyl (CNMe) Ether‐Protected Glycosyl Trichloroacetimidate Donors for Stereoselective β‐O‐Glycosylations DOI
Mosidur Rahaman Molla, Rima Thakur,

Anjali Aghi

и другие.

European Journal of Organic Chemistry, Год журнала: 2023, Номер 26(15)

Опубликована: Март 1, 2023

Abstract Stereoselective construction of glycosidic linkages have emerged as one the pivotal aspects for synthesis complex oligosaccharide assemblies. We herein report C2‐cyanomethyl (CNMe) ether a strong stereodirecting group on trichloroacetimidate glycosyl donors 1,2‐ trans ‐β‐ O ‐glycosides. The developed bearing various arming and disarming protections along with C2‐CNMe delivered glycosides in short reaction time, moderate to good yields high excellent stereoselectivities. Gluco ‐ galacto configured were found compatible an array alcohols having varied reactivities. orthogonality CNMe protection silyl has been further explored sequential glycosylations.

Язык: Английский

Процитировано

3

Photosensitive Fluorous Tag-Assisted Convergent Synthesis of β-1,4-Mannuronates DOI
Yingle Feng, Jie Yang,

Xueqing Fan

и другие.

Organic Letters, Год журнала: 2023, Номер 25(19), С. 3548 - 3552

Опубликована: Май 9, 2023

Rapid synthesis of saccharides by a chemical method is an efficient way to meet the demand for well-defined glycans probe their biological functions. Herein, feasible and convenient strategy saccharide was established introducing photosensitive fluorous tag at anomeric position glycosides. The used not only in polytetrafluoroethylene-assisted rapid purification but also as temporary protecting group reducing end carbohydrates. tag-protected glycosides could be transformed into new glycosyl donors convergent after orthogonal deprotection photolysis. Via combination β-directing C-5 carboxylate glycosylation strategy, β-1,4-mannuronates were efficiently prepared.

Язык: Английский

Процитировано

3

1,4-Naphthoquinone Derivative as Efficient Photolabile Molecule: Concise Synthesis and Photorelease of Various Functional Compounds DOI
Tsuyoshi Kawai, Tsumoru Morimoto, Haiying Liu

и другие.

Synthesis, Год журнала: 2022, Номер 55(01), С. 150 - 158

Опубликована: Авг. 29, 2022

Abstract We report on a series of 1,4-naphthoquinone (NQ)-based photolabile molecules, including various functional compounds to be released under light irradiation. They were efficiently prepared from common precursor for photoremovable masking group, by attaching different such as alcohols, amines, and acids concise synthetic method. Synthesis the was optimized two-step reactions also one-pot reaction involving 1,4-addition successive aldol NQ. The compounds, amines carboxylic, phosphoric, sulfonic acids, masked with NQ-based successfully irradiation UV (λ = 360 nm) in high yields (>90%).

Язык: Английский

Процитировано

2